diff --git a/.github/simili.yaml b/.github/simili.yaml
new file mode 100644
index 000000000..e7b2e0c66
--- /dev/null
+++ b/.github/simili.yaml
@@ -0,0 +1,21 @@
+qdrant:
+  url: "${QDRANT_URL}"
+  api_key: "${QDRANT_API_KEY}"
+  collection: "entireio-cli-issues"
+
+embedding:
+  provider: "gemini"
+  api_key: "${GEMINI_API_KEY}"
+  model: "gemini-embedding-001"
+
+defaults:
+  similarity_threshold: 0.75
+  max_similar_to_show: 5
+
+transfer:
+  duplicate_confidence_threshold: 0.85
+
+repositories:
+  - org: "entireio"
+    repo: "entireio-cli"
+    enabled: true
diff --git a/.github/workflows/simili.yml b/.github/workflows/simili.yml
new file mode 100644
index 000000000..9f448c827
--- /dev/null
+++ b/.github/workflows/simili.yml
@@ -0,0 +1,24 @@
+name: Simili Issue Triage
+
+on:
+  issues:
+    types: [opened, reopened]
+
+jobs:
+  triage:
+    runs-on: ubuntu-latest
+    permissions:
+      issues: write
+      contents: read
+    steps:
+      - uses: actions/checkout@v4
+
+      - name: Run Simili Bot
+        uses: similigh/simili-bot@v0.1.5
+        with:
+          config_path: .github/simili.yaml
+        env:
+          GEMINI_API_KEY: ${{ secrets.GEMINI_API_KEY }}
+          QDRANT_URL: ${{ secrets.QDRANT_URL }}
+          QDRANT_API_KEY: ${{ secrets.QDRANT_API_KEY }}
+          GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
diff --git a/scripts/simili-backfill.sh b/scripts/simili-backfill.sh
new file mode 100755
index 000000000..53132c1b7
--- /dev/null
+++ b/scripts/simili-backfill.sh
@@ -0,0 +1,50 @@
+#!/bin/bash
+# Backfill script for applying Simili Bot triage to existing open issues
+# Usage: ./scripts/simili-backfill.sh
+
+set -euo pipefail
+
+REPO="entireio/cli"
+CONFIG=".github/simili.yaml"
+
+echo "🔍 Fetching open issues from $REPO..."
+
+# Fetch all open issues
+gh issue list --repo "$REPO" --state open --json number,title,body,author,labels,createdAt --limit 1000 > /tmp/issues.json
+
+ISSUE_COUNT=$(jq '. | length' /tmp/issues.json)
+echo "📊 Found $ISSUE_COUNT open issues"
+
+if [ "$ISSUE_COUNT" -eq 0 ]; then
+  echo "✅ No issues to process"
+  exit 0
+fi
+
+echo "🤖 Processing issues with Simili Bot..."
+
+# Process each issue
+jq -c '.[]' /tmp/issues.json | while read -r issue; do
+  NUMBER=$(echo "$issue" | jq -r '.number')
+  TITLE=$(echo "$issue" | jq -r '.title')
+  
+  echo "  Processing #$NUMBER: $TITLE"
+  
+  # Create temporary issue file
+  echo "$issue" > "/tmp/issue-$NUMBER.json"
+  
+  # Run simili process (requires simili CLI to be installed)
+  if command -v simili &> /dev/null; then
+    simili process --issue "/tmp/issue-$NUMBER.json" --config "$CONFIG" || echo "    ⚠️  Failed to process #$NUMBER"
+  else
+    echo "    ⚠️  simili CLI not found. Install with: gh extension install similigh/simili-bot"
+    exit 1
+  fi
+  
+  # Cleanup
+  rm "/tmp/issue-$NUMBER.json"
+  
+  # Rate limit: sleep 2s between issues
+  sleep 2
+done
+
+echo "✅ Backfill complete!"